“RealAudio was greeted with more than a little disdain from the Internet elite because it was a tinny and unsatisfying experience for most users. But it gave the Internet a voice, and Mr. Glaser kept plugging away, improving fidelity and striking deals with more content providers to use it on their Web sites.”

Glaser said that was the simple idea behind Real, to “turn the Web from text and static links to a dynamic media space for the mainstream to enjoy.”

That effort began in earnest in the mid-1990s, he noted, by selling “tech enablement,” which simply meant hawking servers and software to companies interested in adding audio and, later, video, to their Web sites.

So successful was Real then that many big companies tried to buy it for huge sums. But ever the aggressive entrepreneur, Glaser never sold–unlike Mark Cuban at Broadcast.com–although many wished he had.

But that was simply not his style, he said; plus, business was booming and it was “like selling pickaxes during the Gold Rush.”

It is an apt metaphor since the next major moment for the company came when the Web 1.0 bubble burst in 2000.

“A lot of great–and also not so great–companies just died,” he said.

To avoid that fate, “We pivoted in a hard way to consumer services and avoided the tailspin,” Glaser added. “It was kind of like when the woolly mammoth evolved into an elephant, while the pterodactyl did not turn into anything.”

That meant creating a variety of consumer-focused media offerings that used Real technology, such as its casual games business and its Rhapsody music service.

Real also shifted its tech licensing business to a carrier services model, Glaser said.

He regularly tangled with Microsoft (MSFT), where he started his career as a very brash 21-year-old. The software giant targeted Real’s business, but also cooperated with the company at times.

And, while the games unit and Rhapsody hit some major bumps, Real did score a whopping $761 million antitrust settlement in 2005 from Microsoft.

But that win was some time ago, and Real idled too much, as did its stock, in the following years, even as Glaser plugged away at creating a variety of new businesses and strategies.

Some were off limits, he said when I asked him why he did not come up with a service like YouTube, given Real’s advantages in video early on, noting that his public company could never had created a service that so antagonized Hollywood partners.

But Glaser did just that more recently with one such innovative idea for a “legal” DVD ripper, called RealDVD.

While that specific defeat was not the reason for his leaving RealNetworks, the idea that it was time to bring new blood to the company finally gained traction with investors, the board, employees and, yes, Glaser too.

What the notoriously hard-charging executive–“My intensity sometimes manifested itself in less positive ways,” Glaser conceded in my 1998 interview with him–will do next is anyone’s guess.

Including his own.

Glaser noted that he would remain chairman of Real, although his day-to-day engagement there is now over.

“It is a big transition for me, because I am closing a chapter I have been in for a very long time,” he said, adding that he would probably do more philanthropic and political work.

(That’s no surprise. After all, Real was once called Progressive Networks, after his liberal politics, and Glaser once had a newspaper column called “What’s Left” while at Yale University.)

Glaser said that on the flight to Washington he thought about the advice Lotus founder Mitch Kapor, one of Real’s earliest investors, gave him when he left Microsoft and was thinking about his next step:

You should take time to figure out what you want to do next and know why you want to do it. Because if it’s successful, once you get going you won’t have time to think through those issues as clearly as you can now.

That’s pretty much been Glaser’s modus operandi over his many years at Real and in the larger Internet space: He pushed his vision of a live Internet forth, he never cut and ran, he never sold, he kept pushing forward.

And you have to admire that kind of gumption, no matter the outcome.

In any case, it is likely Glaser will keep doing so in the years to come.

In fact, pointing out that the movement of entertainment and content online has “come a long way, but still has an even longer way to go,” Glaser started rattling off ideas about where the online media sector needs to go in exactly the same fashion I described a dozen years before.

I described Glaser then as: “speaking in staccato bursts and radiating so much intensity that his face resembles a clenched fist.”

In other words, for all the the lively entrepreneur has been part of as a key pioneer in the development of the Internet, some things will never ever change.

If you want to see Glaser in action, check out these three videos of him, two from the fifth D: All Things Digital conference and one of him talking to me about RealDVD when he introduced it at Demo:

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